omadacycline   Click here for help

GtoPdb Ligand ID: 10839

Synonyms: amadacycline | compound 6 [PMID: 21302930] | Nuzyra® | PTK-0796 | PTK0796
Approved drug
omadacycline is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Omadacycline (PTK-0796) is an oral, tetracycline-like antibiotic [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 6
Rotatable bonds 7
Topological polar surface area 176.66
Molecular weight 556.29
XLogP 2.54
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@@H]1Cc3c(cc(c(c3C(=C1C2=O)O)O)CNCC(C)(C)C)N(C)C)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[C@@H]1Cc3c(cc(c(c3C(=C1C2=O)O)O)CNCC(C)(C)C)N(C)C)O)O)C(=O)N)C
InChI InChI=1S/C29H40N4O7/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
InChI Key VJYKVCURWJGLPG-IQZGDKDPSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018))
IUPAC Name Click here for help
(4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
9186 omadacycline
Synonyms Click here for help
amadacycline | compound 6 [PMID: 21302930] | Nuzyra® | PTK-0796 | PTK0796
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 246
Other databases
CAS Registry No. 389139-89-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL1689772
GtoPdb PubChem SID 405560280
PubChem CID 54697325
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